


date.

by ruzekhalstead



Series: halstead & upton one-shots. [14]
Category: Chicago PD (TV)
Genre: F/M, Intelligence Boys Friendship, Jealous Jay, Molly's (Chicago Fire), One Chicago (Chicago Franchise), Upstead
Language: English
Status: Completed
Published: 2020-09-03
Updated: 2020-09-03
Packaged: 2021-03-06 16:14:48
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,511
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26261743
Author URL: https://archiveofourown.org/users/ruzekhalstead/pseuds/ruzekhalstead
Summary: “i’m sorry; are we here to distract me or sit around and talk about our feelings?”-prompt: hailey is going on a date and jay is in severe need of a distraction. he calls on his intelligence boys for a guy's night, but that's all forgotten when hailey shows up after her date.
Relationships: Jay Halstead & Hailey Upton, Jay Halstead/Hailey Upton
Series: halstead & upton one-shots. [14]
Series URL: https://archiveofourown.org/series/1634428
Comments: 8
Kudos: 37





	date.

it starts as a day like any other. it’s early, most of the team has just gotten in, and jay is in the break room getting some freshly brewed coffee. there was no open case and voight wasn’t in yet, which meant the unit was catching up on paperwork and anything else they had been avoiding for the past week. 

on his way back to his desk, jay observes vanessa leaning against hailey’s desk, as they chat. with a quick look around the bullpen, he notices kim is nowhere to be found, but he’s sure if she were here, she would be right there with them. 

“i can’t believe you’re going on a date!” vanessa squeals in excitement. 

two things happen in that moment.

hailey rolls her eyes and looks down at the paperwork sitting in front of her and jay trips over his chair and spills his coffee all over his desk. and paperwork. 

vanessa whips around and hailey immediately stands up in shock.

“jay! are you okay?” hailey expresses her concerns, instantly making her way over to his side of the desk and collecting his most precious items so they don’t get destroyed. vanessa escapes into the break room to grab some paper towels. 

jay looks up and makes eye contact with adam, who is smirking like all hell. 

“yeah. shit, sorry,” he apologizes meekly. he’s used to being calm and collected - not nervous and frazzled. vanessa soaks up the coffee with paper towels and although his desk is a little sticky, it’s manageable. “thanks,” he mumbles to vanessa, as they resume their previous positions. 

he attempts to act nonchalant (and like he’s not totally eavesdropping) by organizing his files. 

“can you show me a picture again?”

jay crinkles one of his files by tightening his grip; he’s really trying.

“i already showed you a picture like five times, v!”

jay pales; oh god, they’ve been talking about this for a while, haven’t they?

“i’m sorry, i’m just so excited!” vanessa replies; she seems more excited than hailey is, which piques jay’s interest. “it’s been so long since you last went on a date.”

hailey rolls her eyes again. “yes vanessa, i’m aware of that, thank you.”

“and he’s a successful lawyer! like way to go off with a bang!”

jay fights the urge to roll his eyes this time. a lawyer? come on, hailey. 

“if you ask me,” adam interrupts by rolling back on his chair and stuffing himself between the two detectives, “she will never do better than her ex, but that’s just my opinion.”

hailey replies by aiming a punch at his crotch, but adam is too quick (and honestly, he’s probably expecting it; with his lack of a filter, it can’t be the first time).

“where are you guys going?” vanessa continues the conversation as if adam never interrupted. 

hailey continues filling in her paperwork. “we’re just going to grab a drink at a bar downtown. really simple. we’ve only met like twice.”

jay can’t listen anymore; it’s starting to cause him physical pain. 

he stands from his desk abruptly and goes back to the break room with his coffee mug. there were so many emotions swarming his brain, he isn’t even sure what to think. 

he’s interrupted by adam entering the break room. 

“hey buddy,” he greets with a smirk. “how’s it going?” 

“shut up.”

adam pours himself some more coffee, while jay sulks by the window. “you know this could all be easily avoided.”

“i don’t know to what you are referring to.”

adam rolls his eyes. “if you just told her how you felt, she wouldn’t even think twice about going on this date.”

“i do not comprehend the words that are coming out of your mouth.”

at his stubbornness, adam just stares disapprovingly. “fine; you can be like that. i’ll be sure to ask hailey to share the details of her date out loud, in graphic detail.”

jay’s jaw drops at the pure evil smirk gracing adam’s features. what an ass, jay thinks. 

kevin walks in, but stops when he notices the tension in the room. “shit, is this about upton’s date?”

jay throws his arms up in exasperation and bumps his head against the wall, in hopes that it’ll spontaneously knock him out and when he wakes up, it’ll be next week. 

“yeah, it is,” adam replies, handing kevin a mug of coffee (these detectives looooove their coffee). “i keep telling him this is so simple. if he just told her how she felt, she wouldn’t have to go on dates with randoms and i could win my $100 dollars.” 

jay quirks an eyebrow at adam’s words. he doesn’t even look ashamed, while kevin looks a little sheepish. “there is a bet going on about you two, but it really isn’t important.” 

“no, what’s important is you marching in there right now and declaring your love for her,” adam replies, motioning to the bullpen. “and then i can buy drinks tonight with my well earned $100.”

jay knocks his head against the wall again. 

“no,” he mumbles. 

“what’s that?” adam quirks an eyebrow. “you’ll do this for me because you absolutely adore me?” 

jay shakes his head. “nope; this isn’t happening. i am going to avoid my problems,” adam groans, “and we’re going to have a guy’s night tonight.” 

“a guy’s night?” kevin asks, biting his lip. 

jay nods his head. “yes. i need this. this will take my mind off hailey…” he gulps in distaste, “and her date.”

“fine. but you’re buying,” adam replies, clapping jay on the back as he exits. 

jay frowns. “i thought we could each pitch in for a round. do you understand how much you drink?”

“do you want our help or not?” adam smirks, popping his head back in. 

“fine,” jay grumbles. 

adam smirks cheekily, while kevin just shakes his head in amusement. “fantastic. i’m feeling extra thirsty today.” 

“i hate you.”

* * *

the rests of jay’s day continued on smoothly. he didn’t get much of a chance to be alone with hailey and chat, due to their lack of cases. she mostly focused on her paperwork and as much as he adored vanessa (she was adorable, how could anyone not?) she also didn’t leave hailey’s side for the day. too much excitement over hailey’s “get together with a colleague”. jay refused to call it a date, even in his mind. 

instead, adam, kevin and him went straight to molly’s after the end of their shift, because the sooner jay could start drinking, the better. they were on round two (paid by him of course because adam conveniently “forgot” his wallet) when will walked in. he already had a wild smirk in his face, as he made a beeline straight towards them. 

“alright, which one of you idiots called him?” 

adam scoffs. “i don’t even know the chicago med number, much less will’s extension of 3778.”

“once again: i hate you.”

kevin snickers, bumping fists with adam. the two of them were enjoying this far too much. 

“good evening gentlemen! looks like you all got started without me?” will teases, taking off his jacket and stealing a stool next to jay. he flags herrmann down and asks for another round. “add it to jay’s tab,” he says with a wink.

jay merely tips his bottle up in cheers and herrmann just smirks. 

“alright, so why are we here?” will asks, narrowing his eyes at his younger brother.

jay opens his mouth to reply but kevin beats him to it, “upton’s going out on a date tonight.”

“and jay is handling it very well actually,” adam says, much to jay’s surprise. “he only spilled coffee all over his desk when he found out.”

will is laughing and jay is dying inside. he needs to find new friends. 

“i’m sorry; are we here to distract me or sit around and talk about our _feelings_?”

will hands him a fresh new bottle and says, “copy you.”

* * *

it had only been an hour, but boy, they could drink. 

they kept their drink of choice mostly to beers, with adam and kevin venturing out to a few shots. but the more jay drank, the more he realized, he didn’t want to get completely plastered. while they didn’t talk about hailey and what she was doing, she was always in the back of his mind. it was stupid, he knew that. he could just talk to her; he could just tell her how he was feeling. 

however, the idea of him telling hailey how he felt about her seemed equivalent to drinking car battery acid. 

but then he sees a flash of blonde hair enter the bar and his bottle slips from his grip. 

“jay, what the hell?” adam groans, clumsily reaching across the bar to grab some napkins to soak up the spill.

jay is too distracted to care. “hailey,” he chokes out, his mind growing fuzzy. 

“yes, i know. we’re not supposed to talk about her,” he replies, rolling his eyes.

will reaches around jay (who is dumbly staring at his partner making her way over to them) to smack adam’s arms. “no dumbass, it’s _hailey_ ,” he informs him, watching as adam turns around and his mouth falls into an o. “hey hailey, how are you?” he asks politely. 

“hey will, i’m good, thanks. how are you?” 

it’s true that most of them were severely inebriated but even in that state, they could tell that she was full of shit. she was not good. her eyes were tired and her smile was fake, but they couldn’t tell why. 

“good, thanks,” he replies slowly, sizing her up with his eyes. “actually, we were just leaving, right boys?”

kevin shoots her a smile. “yes, we were. because i’ve had a little too much tequila and it’s time for bed.”

“me too,” adam smirks, nearly falling off his stool and grabbing onto hailey’s shoulders to keep upright. “i don’t really need to go home,” he tries to whisper but he’s failing miserably, “we’re just leaving so you and jay can talk.”

jay drops his head against the bar and groans loudly. 

“ooookay,” will laughs, grabbing adam’s arm and transferring his weight onto him from hailey. “kev and i will make sure he gets home safe. goodnight, you two!”

jay keeps his forehead nailed to the bar, even when he hears hailey sit in the stool next to him. 

“jay,” she says quietly.

he automatically lifts his head and looks at her (how can he not? she looks gorgeous). 

“how did your date go?” 

a corner of her lip lifts sadly. “it didn’t.”

“what?” he snaps, much quicker than he should have. he winces but he’s too curious to care. 

hailey absentmindedly begins playing with one of the old beer bottles left on the counter to distract herself; it also helped to not make eye contact with him (his eyes are just too much for her). “yeah, it didn’t end up happening. he never showed.”

“what?” jay repeats again, this time with a bit more edge in his tone. 

the fact that someone stood hailey up (even though he was against this date from the beginning) severely pissed him off. 

“yeah, i don’t know,” she replies sheepishly. 

jay frowns. “what the hell? that’s not okay.”

“it’s fine, jay,” she protests, because of course she does. 

“it’s not fine!” he replies, feeling himself getting riled up. “that’s not okay because you deserve the fucking world.”

hailey looks at him, her big blue eyes staring at him emotionally. 

“god hailey, you deserve so much. you’re the best person i’ve ever known.”

hailey blushes, which is extremely rare, and she doesn’t like it. but it’s jay. 

“you’re drunk, jay,” she mumbles, busying herself with cleaning up the counter. 

jay stops her by grabbing her wrist; her blue eyes turn to him, nervous. “no, i’m not. i’ve never been so sure of myself.”

hailey doesn’t reply.

“i really didn’t want you to go on that date. fuck, i even spilled my coffee because i was so caught off guard.” she’s laughing at him and it puts him more at ease. “i just—god, i am so horrible at expressing my feelings. but i didn’t want you to go on a date, because i don’t want you to go on any dates, with anyone.”

hailey raises an eyebrow. 

“anyone but me, of course.” there. it’s finally out there. “i was so jealous, hailey. i needed the guys to bring me out tonight and distract me so i wouldn’t ping your cell phone and crash your date. honestly, i really did think about it but then i’d have to explain why and _clearly_ i’m so bad at this and you can stop me at any time, please.”

jay finally stops talking, but hailey isn’t saying anything. that makes him nervous. 

“i was wondering how long it would take you to admit your feelings.”

that is definitely not what he was expecting. 

“um, what?”

“i’m not an idiot jay!” she laughs. “you are the least clumsiest person i’ve ever met. the fact that you spilled your coffee right after my date was mentioned was definitely no coincidence.”

jay frowns. “you mean i’m not a master at hiding my emotions?”

“no, you are,” hailey snorts, “but so am i, and it takes one to know one.”

“since i’ve just spilled my heart out to you, what do you have to say to me?” he teases in a light but nervous manner. he can’t tell much from her reaction what she’s feeling. 

she doesn’t say anything, she just stares at him with an unreadable expression.

he’s about to throw in the towel and take everything back, but then she throws herself off her stool and into his body. her lips meet his in a surprise kiss and surprise is an understatement. 

jay’s inebriated brain takes a moment to register what is actually happening, but once he does, he surges forward with a ferocity that nearly knocks him off his own stool. hailey keeps the kiss short and pulls away, but doesn’t move from her newfound spot in between his knees. 

“that was amazing, but i’m going to need some verbal confirmation,” jay teases, unable to tear his eyes away from her sheepish expression and rosy cheeks. he’s sure he’s smiling, but he isn’t sure he’ll be able to stop for the duration of the night. 

hailey leans her forehead against this chest for a moment. “of course i like you, jay. don’t ask me why, i honestly couldn’t tell you.”

“you can’t tease me right now hailey, i am literally on top of the moon,” he says, and it’s too adorable, she can’t do anything but laugh. 

hailey happily nuzzles into the crook of his neck and stands there as he holds her. she’s quiet for several moments, until she sighs and says, “looks like i owe ruzek a hundred bucks."

jay’s eyes widen at the insinuation of her statement, but all he can do is join her in a laugh. 

**Author's Note:**

> omg i had so much fun writing this, you guys don't even understand
> 
> i think this is the longest one shot i've written in a while because IT WAS SO MUCH FUN TO WRITE
> 
> adam. oh adam, i freaking loved writing him in this.. i hope you all enjoyed him as much as i did
> 
> and my bby jay.. such a nice change from serious and angsty jay.. i loved this so much!!! hope you guys did too!!
> 
> and before you ask, yes, i do plan on writing another date on shot where JAY GOES ON A DATE so we can see how hailey handles it.. so look out for that!!!
> 
> i really hope you guys enjoyed this.. please let me know in the comments bc i really really enjoyed it! 
> 
> onto some sad news, i will be starting school again in two weeks (online but still lol) so it may get harder and harder to write so i'm gonna do my best to dish stuff out within these next two weeks!! so if you guys have requests, let me know now!! :)
> 
> anyway, stay safe & enjoy :)


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